The Benefits and Lessons of Writing a Letter to Your Future Self

In this post: My assessment of the expected and unexpected benefits I got from writing a letter to my future self.

This New Year, I got both a gift and a face-slap reality-check from one of my favorite people in the world:


It came in the form of a letter I wrote on Dec 30, 2020 for my future self to read a year later.

You may wonder, like I did, Is writing a letter to your future self a self-centered, cheesy-YA-novel-esque exercise?


But I attempted to justify it to myself—and to my subscribers in Consider This #18—with five potential benefits:

  • A gift I would appreciate getting.
  • A pleasant dose of nostalgia.
  • A better appreciation for how time flies.
  • A lesson on how much I suck at predicting the future.
  • A general sense of direction.

And now, 376 days later, it’s time to assess whether those benefits panned out.

The Expected and Unexpected Benefits and Lessons From My Letter to My Future Self

Expectations Versus Reality

Did I appreciate the gift?

I haven’t looked forward to opening a gift this much since I was a kid.

Verdict: Easy win.

Was it a pleasant dose of nostalgia?

The first part of my letter was about what was going on in my life and what I was feeling at the time I wrote it.

It felt like a mini time trip back to the Orange River, where I wrote it, and into the mind of my younger, more optimistic, less-wise, and child-less self.

Verdict: Success!

Note:The fact that I hand wrote the letter made it feel extra intimate.

Did it give me a better appreciation for how time flies?

Reading the letter and reflecting on the year that had come and gone felt like looking at the bottom of a Dairy Queen blizzard cup:

I wished there was more. I wished it hadn’t disappeared so quickly. I wished I could go back and do it again. And I vowed to take it slower next time (which won’t happen).

Verdict: Bittersweet victory.

Did I learn a lesson on how much I suck at predicting the future?

This was part of the face-slap wake-up call I got from the letter.

My missed predictions on topics I had no influence over—NBA champions, stock performance, global issues—were funny.

But my missed predictions on things more under my control stung. For example, I failed to reach even half of the income, subscriber, and reader numbers I predicted for this blog.

Verdict: Humbling-ly accurate.

Did it give me a general sense of direction?

Since I accomplished less than I had hoped in 2021, it seems my future self letter exercise either set the wrong direction or didn’t motivate me enough.

On the bright side, it has motivated me to learn from my mistakes to do better in 2022.

Verdict: Semi-failure, semi-success.

The Unexpected Benefits

A Swift Kick in the Pants

I thought I had some new ideas in mind for what to pursue in 2022, such as:

Focus on 1st-person storytelling.
Finding mentorship/coaching/masterminds for the blog.
Organizing a camping trip with family/friends in Canada.
Turns out I wrote those exact same ideas last year!

Somehow, I’d completely forgotten about them. So the fact that I’m again thinking about doing them tells me not to put them off any longer.

A Reminder of How Much I’d Grown

In my letter, I recapped my favorite personal developments from 2020. That was heartening to be reminded of. It also got me reviewing how I’d developed 2021.

This perspective encouraged me. While I didn’t reach all the metrics I’d hoped for in the past year, I’d still managed to make praiseworthy progress up my life’s “y-axis”: Growth.

A Desire for More

The letter I wrote last year was an experiment. I wasn’t sure how it’d work out, but:

  1. The investment was minimal, and
  2. It gave me something to blog about.

Now that the results are in, I can say the experiment was a success.

So last week, I made it into a tradition by writing a letter to my 2022 self. And, this time, I plan to do a better job making my plans, goals, and predictions a reality.

That way, when I read the letter a year from now, hopefully it’ll feel less like a slap-in-the-face wake-up call and more like a rewarding fist bump.

What About You?

Would you consider writing to your future self?

If not, what’s holding you back?

And if you’ve done so before, what was your experience? Did you experience similar benefits, or something different?

Speaking of Letters You’ll Benefit From Reading…

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